


Matchmaker, Matchmaker

by Anonymous



Category: Original Work
Genre: Anal Sex, M/M, Magic, Rough Sex, Safe Sane and Consensual, Safewords, Sex Magic, Shapeshifting, Size Kink, insofar as sex with demons is ever safe or sane
Language: English
Status: Completed
Published: 2019-11-12
Updated: 2019-11-12
Packaged: 2021-01-29 08:21:04
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,180
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21407110
Author URL: https://archiveofourown.org/
Summary: Richard is a human size queen. Fortunately, he's able to summon a demon with a thing for tight human asses.
Relationships: demon/human - Relationship
Comments: 9
Kudos: 135
Collections: Abeastjob, Anonymous, Male Slash Flash Exchange 2019





	Matchmaker, Matchmaker

**Author's Note:**

  * For [Ruis](https://archiveofourown.org/users/Ruis/gifts).

Richard tossed the inflatable butt plug off the bed and sighed. No toy was ever big enough. No toy was ever _real_ enough. He was just too much of a size queen. He would have settled for a well-hung friend with benefits, but to keep up his reputation as a wizard, he had to live in a tower way up in the mountains, and it was not exactly good Tinder territory.

A cat-size house-demon scurried out of its hole in the wall to clean up after his party of one. "You can throw that away," Richard told it as it grabbed the butt plug in one tiny clawed hand. As Richard went into the bathroom, three more demons emerged to change his sheets. He knew the room would be squeaky-clean when he emerged... clean and empty.

But in fact one of the demons was loitering when he returned, freshly showered. "Master," she said, bowing, "may this one offer a suggestion?"

"Sure," Richard said, intrigued. The demons weren't under any compulsion that prevented them from speaking, but they usually kept to themselves.

"Master, this one knows of one who is able to change size and shape, and who has a fondness for sex with humans. That one often complains to this one of not being able to find a human with whom such encounters are fully satisfying. This one believes you might satisfy each other. This one would like to introduce you."

Richard laughed, delighted. "By all means, matchmaker," he said. "I will prepare the summoning circle."

He pulled on his best robe, the classy deep blue one with stars and moons embroidered in real gold thread, and went down the stairs, followed by the little house-demon. Her claws clicked on the stone.

Within a few minutes, he had the summoning circle prepared. He handed the demon a piece of paper and a pen; demon names could not be pronounced aloud, and it would be terrible manners to try. "Write the name of your friend for me," he said. The demon scrawled a symbol. Richard's eyebrows rose. "You travel in high circles, little one."

"This one is the fourteenth offspring of one who is twenty-third in line for the throne of Hell, Master."

"I am honored to have you serving in my house, then." It was a good thing he treated his house-demons well. The last thing he needed was a demonic helicopter parent showing up at his door to demand more employment perks for its offspring—or shred him to pieces for being a bad boss.

Richard studied the symbol, considering. Was his strength and skill up to containing a demon of this might?

His cock twitched, deciding him. It wasn't as though he was going to ask for anything the demon wouldn't want to give him.

He carefully chalked the symbol into the appropriate place in the diagram and then completed the circle and chanted the summoning formula.

Hellfire blossomed in the middle of the circle. From it rose a tall, slender figure. When the smoke and flames cleared, Richard locked eyes with quite the most beautiful demon he'd ever seen. He was clearly from one of the many underground oceans of Hell; his hair was seaweed, his scaly skin was a deep, mottled blue, and there was webbing between his fingers and toes. A crown of horns circled his head. His genitals were hidden behind a loincloth of what might have been dolphin or whale skin; otherwise he was naked.

"Greetings," the sea-demon said informally. "For what purpose do you call upon this one?"

"Greetings," Richard replied. "This one has been given to understand by, uh, this other one that you and I—this one may be able to reach an accommodation of mutual benefit." Ugh, that was awful. He was so out of practice speaking Demonglish.

The sea-demon smirked at him, clearly amused by his fumbling. "This one sees you are accompanied by one this one knows. Greetings, friend."

"Greetings!" the house-demon said happily. "This one is delighted to introduce the two of you. This one is of the impression that you will be sexually compatible."

The sea-demon raised an eyebrow. "Really," it said, regarding Richard with new interest. "Do go on."

"This one enjoys sizable penetration," Richard said, doing his best not to sound awkward. "This one has been unable to obtain satisfaction with human partners or, uh, objects, and this one is led to understand that you are similarly unable to obtain satisfaction with partners who cannot accommodate your size."

"That is true," the sea-demon said. "And you think you can?"

"This one is extremely experienced," Richard said without false modesty, "and can also draw upon magic to permit this one's body to tolerate an unusual degree of stretching."

The sea-demon looked positively delighted now. "This one would be most pleased to explore this with you. You have bound this one well; what conditions do you place?"

Richard had put some thought into that. "No harm to me beyond what my body can heal unaided within seven days. No harm to my home or objects or entities in my home. No removing or impeding my ability to speak. When I say 'yellow' you pause; when I say 'red' you stop; when I speak the words of banishment, you return whence you came. And we pursue a goal of mutual pleasure."

"Agreed," the sea-demon said. He spat into his palm.

Taking a deep breath, Richard spat into his palm, reached across the circle, and took the sea-demon's slender blue hand to seal the deal.

With fluids exchanged, the circle permitted the sea-demon to pass. He strolled over to Richard, looked him up and down, and pushed his robe off his shoulders. As the blue satin puddled on the floor, the demon ran his webbed, clawed hands over Richard's chest and sides. "Humans are so soft," he murmured. One hand caressed Richard's cock, which was so hard it ached. "Soft and hard."

Richard tugged away the sea-demon's loincloth, revealing a cock so big it immediately had his mouth watering. Even half-hard it was almost as long as his forearm. He reached out with both hands and began to stroke it to hardness.

"This one is pleased the two of you find each other acceptable," chirped the house-demon. Richard sprang back from the sea-demon, a little guiltily. He'd quite forgotten the house-demon was there. The sea-demon seemed to feel no guilt at all and continued stroking Richard's cock.

"Most acceptable," the sea-demon said. "This one appreciates your efforts."

"Likewise," Richard managed. The feather-light touch was maddening. "Come, friend, let us remove ourselves to my bedroom. It will be considerably more comfortable than this chamber."

As they went up the stairs, Richard took a quick moment to clear his head and cast a damage tolerance spell over himself. It wouldn't do to forget that.

As soon as they were within sight of the bed, the demon all but shoved Richard onto it. Richard let himself be pushed. It was such a pleasure to have someone else there taking the initiative and putting in some effort. He'd been very lonely, he realized as the demon climbed up behind him.

Then the demon began rubbing its hard, enormous cock up and down on the crack of Richard's ass, and he stopped thinking about anything other than the sensation. He couldn't wait to have that cock in his ass—the thought of it had him grinding up against the demon shamelessly. It was going to be like being fucked with a baseball bat. And then maybe the demon would make it bigger inside him! It was the cock of his dreams. He glanced over his shoulder, admiring the contrast of the demon's blue skin and his own golden brown. The cock looked huge from here. He squirmed.

"Hungry, aren't you," the demon said with a smile. "This one will be glad to give you what you want, if you really can take it."

"I can, I can," Richard panted. "Please, yes."

"Do you need lubricant or is that spell enough?"

Usually Richard would have wanted lube regardless, but he could feel the magic humming in him, ready to heal him of any injury, and he didn't want to delay even for the few seconds it would take to get the lube out of the drawer and apply it to the demon's cock. "Just do it," he begged. "Fuck me, please!"

The demon gave a happy growl, gripped Richard's hips, and slowly pressed the first several inches of his dry cock into Richard's ass.

Richard cried out, feeling the glorious pain and delicious stretch. It was so much easier to relax and open up to the intrusion because he knew nothing either of them did could really harm him. The demon's cock was hard and smooth, slightly tapered, and as big around as a soda can. (Richard knew, because he had two dildos that were supposed to be the width of a soda can. The demon cock felt so much better than any pillar of silicone ever could.) It was cool inside him at first, but his body warmed it.

The demon slowly worked his cock into Richard, dragging out and then pressing back in. He felt it bottom out long before its full length was inside him. He'd just opened his mouth to tell the demon to fuck him deeper anyway when he felt the astonishing sensation of the cock changing shape inside of him. Suddenly it was shorter, and his ass was pressed against the demon's belly. Then he felt it get wider... and wider... and _wider_, stretching his ass impossibly far. Was he going to split in half? He was pretty sure he wouldn't; the demon was well compelled to seek his pleasure. "So good," he groaned. "Yes, more, more! Fuck me, yeah—"

The demon obliged him, driving in harder and faster. The scaly skin of his abdomen abraded Richard's ass, and the demon scratched clawed fingers down his back, clearly enjoying the way Richard cried out and writhed as he was impaled on an enormous blue demon cock.

Every time Richard reached down to touch himself, the demon slapped his hand away. After two or three rounds of this, the demon grabbed Richard's wrists and held them behind his back. Richard bucked and whined, enjoying the semblance of helplessness. As long as he had his voice, he could defend himself... if he chose. 

The demon began to pound Richard's ass like a pile driver. He was pretty sure he would eventually come just from the impossible hotness of it. Every time the pain got to be too much, he begged the demon to release him, and the demon tightened his clawed hand around Richard's wrists and fucked him even harder. It really did feel like a baseball bat or a wine bottle, something so impossible that Richard had no way to comprehend what was happening to him. He wept and pleaded, taking care to avoid all his safewords, and the demon kept making his cock expand and then shoving it up into his guts. By now it was bigger than anything Richard had ever taken.

He was very close to coming when the demon pulled his cock completely out of Richard's ass and then slowly, with much effort, pushed it back in. As it rubbed over his prostate, he yelled and bucked and came all over his sheets.

The demon gave a pleased little laugh and pressed Richard down into the mess on his bed, coating his thighs and belly with come. Then it kept fucking him as he cried out, the overstimulation adding to the overload of agony and pleasure. His cock rubbed against the wet sheets and slowly began to harden again, but he had a feeling a second orgasm would be hard to achieve, so he didn't chase it. He just let the demon take his body apart.

At last the demon groaned and pushed deep into Richard. He could feel the demon's cock throbbing as he came, like a second heartbeat in a most unlikely place. 

When he pulled out, blue fluid trickled out and down Richard's thighs. Richard tried to squeeze his hole back to its usual state of tightness, but his ass had been stretched so wide open that he couldn't close it at all. He hoped that ability would return in time. Right now it served as a reminder of the strange and wonderful encounter he'd just had. 

The scratches on his back stung and itched, healing fast. He'd done a good job with the spell, he thought.

The demon made a happy noise and flung himself down on the bed. "Very nice," he said. "This one approves." He poked Richard with a clawed fingertip. "Again?"

Richard buried his face in the pillows. The demon laughed. "Again soon," he amended. "Maybe tomorrow."

_And every day after that_, Richard thought dreamily. _Just not right now._

As he drifted into an endorphin-scented doze, Richard made a mental note to give that house-demon a bonus.


End file.
